Reductive alkylation of p-benzoquinone using mixed organoboranes

DJ Zillman, GC Hincapié, MR Savari, FG Mizori…

Index: Zillman, David J.; Hincapie, Gloria C.; Reza Savari; Mizori, Farhad G.; Cole, Thomas E. Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3033 - 3036

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Citation Number: 6

Abstract

Mixed organoboranes based on diphenyl-or dimethylalkylboranes transfer the alkyl group in the reductive alkylation of p-benzoquinone to form the alkylhydroquinones in very high yields. The auxiliary groups do not transfer or have a low migratory aptitude. Primary and secondary alkyl groups are transferred with retention of regio-and stereochemistry to the hydroquinone. O-Alkylation is the major product with tertiary and secondary groups with ...